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3,5-diaminopyridine and preparation method of 3,5-dimethoxycarboxylaminopyridine

A technology of diaminopyridine and pyridine dicarboxylic acid, applied in 3 fields, can solve the problems of limited application, high price, difficult to obtain, etc., and achieves the effects of expanding the scope of application, convenient removal, and simple processing

Inactive Publication Date: 2011-08-24
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires the use of an expensive Pd / C catalyst, and the synthetic raw material 3,5-dinitro-2-chloropyridine is also very difficult to obtain, which limits its popularization and application

Method used

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  • 3,5-diaminopyridine and preparation method of 3,5-dimethoxycarboxylaminopyridine
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  • 3,5-diaminopyridine and preparation method of 3,5-dimethoxycarboxylaminopyridine

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preparation example Construction

[0027] combine figure 1 , the preparation method of 3,5-diaminopyridine of the present invention, the steps are as follows:

[0028] In the first step, 3,5-lutidine is oxidized to obtain 3,5-pyridinedicarboxylic acid; the oxidizing agent for the oxidation reaction includes potassium permanganate, potassium dichromate, chromium oxide or tin dioxide; the oxidation reaction The temperature is 50-90°C; the molar ratio of oxidation reaction oxidant to 3,5-lutidine is 2:1-5.5:1.

[0029] In the second step, 3,5-pyridinedicarboxylic acid is prepared by acid chlorination reaction to obtain 3,5-pyridine dicarboxylic acid chloride; acid chloride reaction acid chloride reagent is selected from thionyl chloride, phosphorus trichloride or oxalyl chloride; acid chloride reaction temperature 56~65℃; the acid chloride reagent is used as both the reaction reagent and the solvent in the acid chloride reaction, and the acid chloride reagent is in excess of 3,5-pyridine dicarboxylic acid.

[00...

Embodiment 1

[0038] Example 1: Add 5ml of 3,5-lutidine (specific gravity: 0.99) into a three-necked flask filled with 75ml of water, stir and heat up to 40°C, add 29g of potassium permanganate in batches, complete the addition, and react at a constant temperature 2h. Cool to room temperature, filter with suction, adjust the pH of the filtrate to 1.5 to 2.0 with hydrochloric acid, precipitate a white precipitate, filter with suction, wash with 100ml of water, and dry the filter cake to obtain 5g of white powder of 3,5-pyridinedicarboxylic acid with a yield of 65%. m.p.324~326℃; 1 H NMR (DMSO-d 6 , 300MHz); δ: 8.65 (s, 1H, Ar-H), 9.25 (s, 2H, Ar-H), 13.71 (brs, 2H, -COOH); IR, (KBr) v: 3088 (C-H), 2914(O-H), 1720(C=O), 1600(C=C), 1163(C-O), 775(C-H)cm -1 ; Mass Spectrum: MS (ESI) m / z: 165.97 (30), MS / MS: 121.97 (100); it can be determined that the generated substance is 3,5-pyridinedicarboxylic acid.

Embodiment 2

[0039] Example 2: Add 5ml of 3,5-lutidine (specific gravity: 0.99) into a three-necked flask filled with 75ml of water, stir and heat up to 60°C, add 38g of potassium permanganate in batches, complete the addition, and react at a constant temperature 1h. Cool to room temperature, filter with suction, adjust the pH of the filtrate to 1.5-2.0 with hydrochloric acid, precipitate a white precipitate, filter with suction, wash with 100ml of water, and dry the filter cake to obtain 6.16 g of white powder of 3,5-pyridinedicarboxylic acid, yield 79.7 %.

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Abstract

The invention discloses 3,5-diaminopyridine and a preparation method of 3,5-dimethoxycarboxylaminopyridine. The preparation method comprises the following steps: using 3,5-dimethylpyridine to perform oxidation reaction so as to obtain 3,5-pyridinedicarboxylic acid; using 3,5-pyridinedicarboxylic acid to perform acyl chlorination and obtain 3,5-pyridinedicarbonyl chloride; using 3,5-pyridinedicarbonyl chloride to perform ammoniation reaction to obtain 3,5-pyridinedimethylformamide; and performing Hofmann degradation on the 3,5-pyridinedimethylformamide to prepare 3,5-diaminopyridine or 3,5-dimethoxycarboxylaminopyridine. In the invention, 3,5-dimethylpyridine is used as raw material to design the synthetic route of the target compound, the reaction conditions of each step are mild, the product purity and yield are obviously increased, the yield is more than 70%; and the aftertreatment of each step of the provided synthetic route is simple, the method is green and environmentally friendly, the oxidation product is solid manganese dioxide, the oxidation product can be recycled through filtering, and the compound 2 can be used to perform the next step without being separated.

Description

technical field [0001] The invention belongs to the preparation technology of organic synthesis intermediates, in particular to a preparation method of 3,5-diaminopyridine and 3,5-dimethoxycarbonylaminopyridine. Background technique [0002] Aminopyridine and its derivatives are a class of amino-containing nitrogen heterocyclic compounds. It has been found through research that the amino compound obtained by replacing the benzene ring with a pyridine ring has higher biological activity, or lower toxicity, or higher systemic and selectivity. 3,5-diaminopyridine itself is a good hair coloring agent, and as an organic synthesis intermediate, it is widely used in the synthesis of fine chemicals such as medicine, pesticides, dyes, and functional materials. For example, 3,5-diaminopyridine can replace aniline for the synthesis of polyamides as outsourcing materials such as microelectronic circuits and aerospace, and the thermal stability of such polyamides is significantly enhanc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73C07D213/75
Inventor 胡炳成刘祖亮梁长玉戴红升孙呈郭徐士超
Owner NANJING UNIV OF SCI & TECH
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